C1,C2-ether derivatives of the Amaryllidaceae alkaloid lycorine: retention of activity of highly lipophilic analogues against cancer cells

Bioorg Med Chem Lett. 2014 Feb 1;24(3):923-7. doi: 10.1016/j.bmcl.2013.12.073. Epub 2013 Dec 24.

Abstract

As a continuation of the studies aimed at the development of new anticancer agents derived from the Amaryllidaceae alkaloid lycorine, 35 C1,C2-ether analogues of this natural product were synthesized. The compounds were evaluated for antiproliferative activities in vitro in a panel of tumor cell lines with varied levels of apoptosis resistance. A strong correlation between the compound lipophilicity and anticancer activity was observed, indicating that cell permeability properties must be an important determinant in the design of lycorine-based anticancer agents. A theoretical docking model, consistent with the experimental observations, is presented.

Keywords: Alkaloid; Apoptosis resistance; Cancer; Glioblastoma; Melanoma.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Amaryllidaceae Alkaloids / chemistry*
  • Amaryllidaceae Alkaloids / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects*
  • Binding Sites
  • Cell Line, Tumor
  • Computer Simulation
  • Ethers / chemistry*
  • Ethers / pharmacology*
  • Humans
  • Liliaceae / chemistry*
  • Lipids / chemistry
  • Models, Molecular
  • Molecular Structure
  • Phenanthridines / chemistry*
  • Phenanthridines / pharmacology
  • Solubility

Substances

  • Alkaloids
  • Amaryllidaceae Alkaloids
  • Antineoplastic Agents
  • Ethers
  • Lipids
  • Phenanthridines
  • lycorine